Enterprise Systems Practitioner

Technology is no longer just an enabler of business strategy. It is the business strategy. And with AI reshaping how companies operate, compete and grow — while rapidly accelerating the pace of change — the stakes have never been higher.

We’re focused on helping private equity investors and portfolio company leaders drive value creation through technology. In a world where investors deploy trillions annually into software and tech-enabled businesses, we're the team that makes sure the underlying technology actually delivers.

The expert judgment of our experienced practitioners is complemented by proven frameworks, tech-enabled solutions, and objective data to help organizations navigate critical technology decisions across diligence, transformation, growth, cybersecurity, AI, and operational execution.

Everything we do is grounded in five core values: Service. Curiosity. Credibility. Commitment. Creativity.

If you're energized by solving complex technology challenges and helping others succeed in critical moments by providing insight and clarity, you'll fit right in.

About the role

We are looking for an Enterprise Systems Practitioner to lead diligence and/or value creation engagements.  Diligence engagements include sell-side and buy-side across the enterprise systems, traditional and hybrid infrastructure, managed services, and critical business processes that support business operations. Most initial assignments will be transaction-focused and move at deal speed.

Value creation engagements include developing a systems roadmap, evaluating enterprise applications, leading a platform or provider selection, governing a critical programme, or serving as an interim or fractional systems leader.

In all engagements, you will assess how processes work in practice; determine whether the systems, data, controls, operating procedures, and third-party services are fit for purpose; and translate your findings into clear conclusions for investors and management teams.

Role responsibilities

• Lead sell-side technology diligence, including evidence review, management interviews, buyer-readiness assessment, remediation priorities, and support for buyer questions.
• Lead buy-side technology diligence and assess the systems estate, infrastructure, organisation, vendors, contracts, spend, scalability, resilience, and investment requirements.
• Evaluate ERP, warehouse and WMS environments and the finance, procurement, order management, inventory, fulfilment, and warehouse processes they support, including process fit, customisation, integrations, data quality, reporting, controls, manual workarounds, vendor support, licensing, lifecycle risk, and replacement or upgrade exposure.
• Evaluate front- and mid-office systems like CRM and PSA, and the lead-to-cash and project-to-cash processes they support, including opportunity management, resource planning, project delivery, time and expense, billing, project accounting, revenue recognition, customer data, adoption, controls, and reporting.
• Assess critical end-to-end business processes, including order-to-cash, procure-to-pay, record-to-report and month-end close, recruit-to-retire, and other sector-relevant processes. Use process walkthroughs, management and user interviews, system evidence, reports, and operating metrics to identify weak handoffs, control gaps, manual workarounds, data issues, key-person dependencies, and scalability constraints.
• Assess data centres, colocation, networks, identity, end-user computing, backup, disaster recovery, hybrid cloud, and the practical migration of traditional COTS systems to IaaS or limited PaaS environments.
• Assess MSP and MSSP arrangements, including service scope, pricing, contracts, service levels, operating performance, transition risk, and governance. Lead provider selection or remediation when requested.
• Evaluate IT operating procedures, including service desk operations, service requests, incident, problem and change management, user onboarding and offboarding, access management, asset and configuration management, escalation, service levels, and operational reporting, whether delivered internally or through an MSP or MSSP.
• Identify and size material one-time and recurring investments, including deferred upgrades, system replacement, infrastructure remediation, provider transition, and additional staffing or capability needs.
• Translate technical and operational findings into concise, evidence-based conclusions that are relevant to the investment thesis and understandable to senior non-technical stakeholders.
• Develop practical post-close systems roadmaps and, where appropriate, help clients select vendors, govern delivery, improve operating discipline, or fill an interim leadership gap.
• Work with Crosslake specialists in cybersecurity, data and AI, product and software, integration, and carve-out services when an engagement requires deeper domain expertise.
• Contribute to Crosslake methods, benchmarks, training, and service development based on your operating and client experience.

• You identify the few business-process, systems, data, infrastructure, supplier, control, and cost issues that can materially affect a transaction or value-creation plan.
• You distinguish symptoms from root causes and determine whether an operational problem is primarily driven by process design, system fit, data, controls, organisation, training, governance, or service-provider performance.
• Your reports are clear, concise, defensible, and useful to investment committees, operating partners, boards, and management teams.
• You work effectively with incomplete information, make uncertainty explicit, and know which questions or evidence will change the conclusion.
• You move quickly without relying on a checklist or sacrificing judgment.
• You can lead an engagement independently while drawing in colleagues when another specialist will improve the answer.
• When work continues after close, your recommendations translate into an executable roadmap with clear owners, costs, priorities, and outcomes.

What we’re looking for

• At least 15 years of relevant experience in enterprise systems, IT operations, technology leadership, systems transformation, transaction advisory, or a combination of these fields.
• Experience leading multiple sell-side, buy-side, or comparable rapid technology assessments for private-equity, corporate M&A, or portfolio-company clients.
• Leadership-level knowledge across ERP and warehouse systems, PSA, CRM, and traditional infrastructure and managed services.
• Deep operating or delivery experience in at least two of those three areas.
• Direct accountability for major business-process or systems outcomes, transformation programmes, budgets, service providers, or IT operations.
• Demonstrated ability to conduct process walkthroughs and assess end-to-end business processes across multiple functions, with direct experience in several of order-to-cash, project-to-cash, procure-to-pay, record-to-report and month-end close, recruit-to-retire, warehouse and fulfilment operations, and IT service management.
• Experience selecting, implementing, upgrading, recovering, or rationalising enterprise systems, supported by a practical understanding of process and data dependencies.
• Experience with traditional and hybrid infrastructure, including data-centre or colocation environments and migrations of packaged applications to cloud infrastructure.
• Experience selecting, transitioning, managing, or materially renegotiating MSP or MSSP services.
• Strong analytical and financial judgment, including the ability to estimate one-time and recurring technology investments.
• Excellent written and verbal communication with investors, boards, executives, functional leaders, and technical teams.
• A self-directed and hands-on working style suited to fast-moving, remote client engagements.

• Former CIO, VP of IT, Head of Enterprise Applications, enterprise systems programme leader, technology operating partner, or senior M&A technology advisor.
• Experience in professional services, technology-enabled services, distribution, logistics, manufacturing, or other sectors where enterprise systems directly affect revenue and operational delivery.
• Experience with Salesforce and industry-relevant PSA and professional-services platforms.
• Experience with WMS and warehouse operations, with eCommerce exposure as an additional advantage.
• Experience converting diligence findings into systems roadmaps, vendor selections, implementation governance, or interim leadership assignments.
• A bachelor's degree in information systems, computer science, engineering, business, or a related field. Relevant experience matters more than a specific degree or certification.